Pyridine → HCID 20083178, compound

HRID 1656763Notes

Reaction equation

HRID 1656763 reaction equation
[F:1][C:2]1[C:3](OS(C2C=CC(C)=CC=2)(=O)=O)=[C:4]2[C:9]3=[C:10]([C:12](=[O:19])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:8]3[N:7]([CH3:20])[CH2:6][CH2:5]2)[CH:11]=1.N1C=CC=CC=1.FC(F)(F)S([O:43][S:44]([C:47]([F:50])([F:49])[F:48])(=[O:46])=[O:45])(=O)=O>C(Cl)(Cl)Cl>[F:1][C:2]1[C:3]([O:43][S:44]([C:47]([F:48])([F:49])[F:50])(=[O:45])=[O:46])=[C:4]2[C:9]3=[C:10]([C:12](=[O:19])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:8]3[N:7]([CH3:20])[CH2:6][CH2:5]2)[CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 19788676HCID 19788676, compound

Product 1

HCID 20083178HCID 20083178, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.8 g of the compound (169) obtained in Example 46 was added to 10 ml of pyridine, and while cooling on ice, 2.35 ml of trifluoromethanesulfonic anhydride was added to the solution through 20 minutes. The solution was stirred for 24 hours at room temperature. 200 ml of chloroform was added to the solution, and the solution was washed with aqueous 5% citric acid solution. The organic layer was separated and after drying over magnesium sulfate, the solvent was removed by distillation. To the residue, ethanol was added, and the solid matter was filtered off and purified by column chromatography (silica gel, eluent solvent; chloroform:ethyl acetate=1:1). The solid matter was filtered off and washed with isopropyl ether to obtain 1.2 g of the subject compound (170).

Workup

  1. additionwas added to the solution through 20 minutes
  2. washthe solution was washed with aqueous 5% citric acid solution
  3. customThe organic layer was separated
  4. dry with materialafter drying over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. additionTo the residue, ethanol was added
  7. filtrationthe solid matter was filtered off
  8. custompurified by column chromatography (silica gel, eluent solvent; chloroform:ethyl acetate=1:1)
  9. filtrationThe solid matter was filtered off
  10. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-b3c76985c8db4598b8b24f3a87da89b0
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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